Poly[(acetato-κ2O,O′)aqua­(μ4-1H-benzimidazole-5,6-dicarboxyl­ato-κ5N3:O5,O5′:O5,O6:O6′)praseodymium(III)]

Pan, Z.-Y.; Chen, J.-H.; Lin, J.-F.; Xu, X.; Luo, Y.-F.

doi:10.1107/S1600536810036986

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page m1302

doi:10.1107/S1600536810036986

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Poly[(acetato-κ²O,O′)aqua(μ₄-1H-benzimidazole-5,6-dicarboxylato-κ⁵N³:O⁵,O^5′:O⁵,O⁶:O^6′)praseodymium(III)]

Zi-Yu Pan,^a Jin-Hua Chen,^a Jian-Fen Lin,^a Xuan Xu ^a ^* and Yi-Fan Luo ^a

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China
^*Correspondence e-mail: xuxuan2004@yahoo.com.cn

(Received 20 August 2010; accepted 15 September 2010; online 25 September 2010)

In the title complex, [Pr(C₉H₄N₂O₄)(C₂H₃O₂)(H₂O)]_n, the Pr^III ion is coordinated by five O atoms and one N atom from four benzimidazole-5,6-dicarboxylate ligands, two O atoms from an acetate ligand and one water molecule, giving a tricapped trigonal-prismatic geometry. The benzimidazole-5,6-dicarboxylate and acetate ligands connect the Pr^III ions, forming a layer in the ac plane; the layers are further linked by N—H⋯O and O—H⋯O hydrogen bonding and π–π stacking interactions between neighboring pyridine rings [the centroid–centroid distance is 3.467 (1) Å], assembling a three-dimensional supramolecular network. The acetate methyl group is disordered over two positions with site-occupancy factors of 0.75 and 0.25.

Related literature

For related structures, see: Gao et al. (2008 ); Lo et al. (2007 ); Wang et al. (2009 ); Wei et al. (2008 ); Yao et al. (2008 ); Zhai (2009 ).

Experimental

Crystal data

[Pr(C₉H₄N₂O₄)(C₂H₃O₂)(H₂O)]
M_r = 422.11
Triclinic, $[P \overline 1]$
a = 7.4284 (5) Å
b = 9.0109 (7) Å
c = 9.7239 (7) Å
α = 87.075 (1)°
β = 86.498 (1)°
γ = 84.274 (1)°
V = 645.77 (8) Å³
Z = 2
Mo Kα radiation
μ = 3.81 mm⁻¹
T = 296 K
0.26 × 0.22 × 0.19 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.386, T_max = 0.485
3963 measured reflections
2327 independent reflections
2184 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.072
S = 1.04
2327 reflections
199 parameters
22 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.23 e Å⁻³
Δρ_min = −1.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O6ⁱ	0.85 (2)	1.90 (3)	2.712 (5)	159 (5)
O1W—H1W⋯O2ⁱⁱ	0.83 (2)	2.06 (3)	2.854 (4)	159 (6)
O1W—H2W⋯O5ⁱⁱⁱ	0.84 (2)	1.96 (2)	2.794 (4)	176 (5)
Symmetry codes: (i) x-1, y, z+1; (ii) x+1, y, z; (iii) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810036986/pk2264sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810036986/pk2264Isup2.hkl

checkCIF report

Comment top

In recent years, studies of coordination polymers built using metals and multifunctional organic ligands, has been a rapidly expanding field. This has been due to their intriguing structural motifs and functional properties, such as molecular adsorption, magnetism, and luminescence. Benzimidazole-5,6-dicarboxylic acid (H₂L) is such a multifuctional ligand with both nitrogen and oxygen donor atoms (Gao et al., 2008; Lo et al., 2007; Wang et al., 2009; Wei et al., 2008; Yao et al., 2008; Zhai et al., 2009). For example, Yao and co-workers have successfully synthesized six novel two-dimensional coordination polymers based on this ligand, namely, [MnL]_n (1), {[Ni₂L₂(H₂O)₄].(H₂O)₃}_n (2), {[Tb(L)(HL)(H₂O)].(H₂O)}_n (3) and {[Ln₂L₂(HL)₂(H₂O)₂]}_n (Ln=Ho (4), Er (5), Lu (6)) (Yao et al., 2008). Wei et al. also obtained a novel five coordinated Mn(II) polymer ([Mn(HL)])_n possessing abundant hydrogen bonds and π-π stacking interactions (Wei et al., 2008). Herein, we report the hydrothermal synthesis, structure of the novel coordination polymer.

In the structure of the title compound (Fig. 1), each Pr^III centre is nine-coordinated by five oxygen atoms and one N atom from four benzimidazole-5,6-dicarboxylato ligands, two oxygen atoms from an acetate ligand, and one water molecule. The structure can described as having a bicapped trigonal prismatic geometry with Pr···O distances and O···Pr···O angles ranging from 2.373 (3) Å to 2.645 (3) Å and 69.84 (9) ° to 152.88 (1) °, respectively. The benzimidazole-5,6-dicarboxylate and acetate ligands, act as bridging ligands, linking the Pr^III metal centres into a layer parallel to the ac plane (Fig. 2). Those layers are further connected via O—H···O and N—H···O hydrogen bonding interactions (Table 1) to form a three-dimensional supramolecular motif, which is stabilized by π-π stacking interactions between neighboring pyridyl rings (the centroid···centroid distance is 3.467 (1) Å).

Related literature top

For related structures, see: Gao et al. (2008); Lo et al. (2007); Wang et al. (2009); Wei et al. (2008); Yao et al. (2008); Zhai et al. (2009).

Experimental top

A mixture of Pr₆O₁₁ (0.170 g; 0.17 mmol), benzimidazole-5,6-dicarboxylic acid (0.206 g; 1 mmol), acetic acid (0.06 g; 1 mmol), water (10 ml) was stirred vigorously for 30 min and then sealed in a teflon-lined stainless-steel autoclave (20 ml, capacity). The autoclave was heated and maintained at 423 K for 3 days, and then cooled to room temperature at 5 K h^-1, which produced colorless block-shaped crystals.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound, together with some symmetry related atoms to complete the coordination units. Displacement ellipsoids drawn at the 50% probability level. [Symmetry codes: (#1) x, y, -1+z; (#2) -x, 1-y, -z; (#3) 1-x, 1-y, -z.]
	Fig. 2. A view of the layers parallel to the ac plane.

Poly[(acetato-κ²O,O')aqua(µ₄-1H- benzimidazole-5,6-dicarboxylato- κ⁵N³:O⁵,O^5':O⁵,O⁶: O^6')praseodymium(III)] top

Crystal data top

[Pr(C₉H₄N₂O₄)(C₂H₃O₂)(H₂O)]	Z = 2
M_r = 422.11	F(000) = 408
Triclinic, P1	D_x = 2.171 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4284 (5) Å	Cell parameters from 2989 reflections
b = 9.0109 (7) Å	θ = 2.3–28.4°
c = 9.7239 (7) Å	µ = 3.81 mm⁻¹
α = 87.075 (1)°	T = 296 K
β = 86.498 (1)°	Block, colourless
γ = 84.274 (1)°	0.26 × 0.22 × 0.19 mm
V = 645.77 (8) Å³

Data collection top

Bruker SMART APEX CCD diffractometer	2327 independent reflections
Radiation source: fine-focus sealed tube	2184 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω scans	θ_max = 25.2°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −8→8
T_min = 0.386, T_max = 0.485	k = −10→10
3963 measured reflections	l = −7→11

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.072	w = 1/[σ²(F_o²) + (0.0394P)² + 1.0511P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
2327 reflections	Δρ_max = 1.23 e Å⁻³
199 parameters	Δρ_min = −1.45 e Å⁻³
22 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0091 (12)

Crystal data top

[Pr(C₉H₄N₂O₄)(C₂H₃O₂)(H₂O)]	γ = 84.274 (1)°
M_r = 422.11	V = 645.77 (8) Å³
Triclinic, P1	Z = 2
a = 7.4284 (5) Å	Mo Kα radiation
b = 9.0109 (7) Å	µ = 3.81 mm⁻¹
c = 9.7239 (7) Å	T = 296 K
α = 87.075 (1)°	0.26 × 0.22 × 0.19 mm
β = 86.498 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	2327 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2184 reflections with I > 2σ(I)
T_min = 0.386, T_max = 0.485	R_int = 0.028
3963 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	22 restraints
wR(F²) = 0.072	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 1.23 e Å⁻³
2327 reflections	Δρ_min = −1.45 e Å⁻³
199 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Pr1	0.35344 (3)	0.35784 (2)	−0.10574 (2)	0.01137 (13)
O1	0.1245 (4)	0.2800 (3)	0.0551 (3)	0.0171 (6)
O1W	0.6206 (5)	0.2207 (4)	0.0136 (4)	0.0286 (8)
H1W	0.713 (5)	0.260 (5)	0.032 (6)	0.034*
H2W	0.626 (7)	0.135 (3)	0.051 (6)	0.034*
O2	−0.1348 (4)	0.4123 (3)	0.1093 (3)	0.0187 (7)
O3	0.5275 (4)	0.4696 (4)	0.2957 (3)	0.0229 (7)
O4	0.3620 (4)	0.4864 (3)	0.1165 (3)	0.0169 (6)
O5	0.3704 (4)	0.0699 (3)	−0.1295 (3)	0.0213 (7)
O6	0.5234 (4)	0.2005 (3)	−0.2842 (3)	0.0222 (7)
N1	−0.1290 (5)	0.2444 (4)	0.6358 (4)	0.0197 (8)
H1	−0.237 (4)	0.219 (6)	0.642 (6)	0.024*
N2	0.1301 (5)	0.3045 (4)	0.7108 (4)	0.0183 (8)
C1	0.0176 (5)	0.3514 (4)	0.1395 (4)	0.0124 (8)
C2	0.0663 (5)	0.3516 (4)	0.2883 (4)	0.0128 (8)
C3	−0.0669 (6)	0.3032 (5)	0.3815 (5)	0.0179 (9)
H3	−0.1780	0.2820	0.3522	0.021*
C4	−0.0292 (5)	0.2876 (5)	0.5200 (5)	0.0158 (9)
C5	0.1336 (5)	0.3240 (4)	0.5684 (4)	0.0137 (8)
C6	0.2660 (5)	0.3744 (4)	0.4746 (4)	0.0138 (8)
H6	0.3747	0.3995	0.5056	0.017*
C7	0.2352 (5)	0.3872 (4)	0.3345 (4)	0.0121 (8)
C8	0.3828 (5)	0.4492 (4)	0.2436 (4)	0.0117 (8)
C9	−0.0292 (6)	0.2583 (5)	0.7442 (5)	0.0191 (9)
H9	−0.0696	0.2371	0.8348	0.023*
C10	0.4743 (7)	0.0768 (5)	−0.2356 (6)	0.0304 (9)
C11	0.5650 (11)	−0.0621 (7)	−0.2989 (8)	0.0304 (9)	0.75
H11A	0.6777	−0.0907	−0.2569	0.046*	0.75
H11B	0.5877	−0.0431	−0.3961	0.046*	0.75
H11C	0.4876	−0.1412	−0.2840	0.046*	0.75
C11'	0.477 (3)	−0.055 (2)	−0.332 (2)	0.0304 (9)	0.25
H11D	0.5368	−0.1430	−0.2891	0.046*	0.25
H11E	0.5413	−0.0309	−0.4178	0.046*	0.25
H11F	0.3551	−0.0717	−0.3491	0.046*	0.25

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pr1	0.01163 (17)	0.01259 (17)	0.00993 (17)	−0.00185 (9)	0.00044 (10)	−0.00098 (10)
O1	0.0192 (15)	0.0188 (15)	0.0137 (16)	−0.0041 (12)	0.0014 (12)	−0.0035 (12)
O1W	0.0286 (18)	0.0164 (16)	0.042 (2)	−0.0047 (14)	−0.0170 (16)	0.0049 (15)
O2	0.0167 (15)	0.0199 (15)	0.0190 (17)	0.0033 (12)	−0.0052 (13)	−0.0022 (13)
O3	0.0175 (16)	0.0315 (18)	0.0207 (18)	−0.0097 (13)	−0.0023 (13)	0.0039 (14)
O4	0.0200 (15)	0.0180 (15)	0.0131 (16)	−0.0055 (12)	0.0002 (12)	0.0008 (12)
O5	0.0240 (16)	0.0159 (15)	0.0239 (18)	−0.0040 (12)	0.0013 (14)	−0.0006 (13)
O6	0.0206 (16)	0.0198 (16)	0.0252 (18)	−0.0003 (12)	0.0048 (13)	−0.0019 (13)
N1	0.0150 (18)	0.029 (2)	0.016 (2)	−0.0078 (15)	0.0018 (15)	0.0025 (16)
N2	0.0203 (19)	0.0214 (18)	0.0130 (19)	−0.0036 (15)	0.0017 (15)	−0.0006 (15)
C1	0.0136 (19)	0.0106 (18)	0.013 (2)	−0.0035 (15)	0.0002 (16)	0.0017 (16)
C2	0.0128 (19)	0.0126 (19)	0.013 (2)	−0.0012 (15)	−0.0005 (16)	−0.0008 (16)
C3	0.014 (2)	0.022 (2)	0.018 (2)	−0.0019 (17)	−0.0023 (17)	−0.0015 (18)
C4	0.013 (2)	0.019 (2)	0.015 (2)	−0.0007 (16)	0.0010 (17)	−0.0014 (17)
C5	0.015 (2)	0.0135 (19)	0.012 (2)	−0.0001 (15)	0.0013 (16)	−0.0017 (16)
C6	0.0109 (19)	0.0138 (19)	0.017 (2)	−0.0015 (15)	0.0002 (16)	−0.0017 (17)
C7	0.0126 (19)	0.0108 (18)	0.013 (2)	−0.0006 (15)	0.0012 (16)	−0.0015 (16)
C8	0.015 (2)	0.0105 (18)	0.010 (2)	−0.0011 (15)	−0.0008 (16)	−0.0011 (15)
C9	0.022 (2)	0.025 (2)	0.010 (2)	−0.0049 (18)	0.0024 (17)	0.0032 (18)
C10	0.037 (2)	0.0221 (19)	0.031 (2)	0.0040 (18)	0.0026 (19)	−0.0054 (17)
C11	0.037 (2)	0.0221 (19)	0.031 (2)	0.0040 (18)	0.0026 (19)	−0.0054 (17)
C11'	0.037 (2)	0.0221 (19)	0.031 (2)	0.0040 (18)	0.0026 (19)	−0.0054 (17)

Geometric parameters (Å, º) top

Pr1—O1	2.373 (3)	N2—C9	1.310 (6)
Pr1—O6	2.498 (3)	N2—C5	1.386 (6)
Pr1—O2ⁱ	2.501 (3)	N2—Pr1^iv	2.603 (4)
Pr1—O4	2.511 (3)	C1—C2	1.512 (6)
Pr1—O3ⁱⁱ	2.528 (3)	C2—C3	1.389 (6)
Pr1—O1W	2.541 (3)	C2—C7	1.429 (6)
Pr1—N2ⁱⁱⁱ	2.603 (4)	C3—C4	1.389 (6)
Pr1—O5	2.606 (3)	C3—H3	0.9300
Pr1—O4ⁱⁱ	2.646 (3)	C4—C5	1.399 (6)
Pr1—C8ⁱⁱ	2.963 (4)	C5—C6	1.394 (6)
O1—C1	1.261 (5)	C6—C7	1.393 (6)
O1W—H1W	0.833 (19)	C6—H6	0.9300
O1W—H2W	0.836 (19)	C7—C8	1.499 (6)
O2—C1	1.253 (5)	C8—Pr1ⁱⁱ	2.963 (4)
O2—Pr1ⁱ	2.501 (3)	C9—H9	0.9300
O3—C8	1.250 (5)	C10—C11	1.503 (8)
O3—Pr1ⁱⁱ	2.528 (3)	C10—C11'	1.55 (2)
O4—C8	1.278 (5)	C11—H11A	0.9600
O4—Pr1ⁱⁱ	2.646 (3)	C11—H11B	0.9600
O5—C10	1.253 (6)	C11—H11C	0.9600
O6—C10	1.267 (6)	C11'—H11D	0.9600
N1—C9	1.342 (6)	C11'—H11E	0.9600
N1—C4	1.372 (6)	C11'—H11F	0.9600
N1—H1	0.85 (2)

O1—Pr1—O6	125.76 (10)	C10—O6—Pr1	96.4 (3)
O1—Pr1—O2ⁱ	79.97 (10)	C9—N1—C4	107.0 (4)
O6—Pr1—O2ⁱ	135.37 (10)	C9—N1—H1	125 (4)
O1—Pr1—O4	69.81 (9)	C4—N1—H1	128 (4)
O6—Pr1—O4	147.25 (10)	C9—N2—C5	104.1 (4)
O2ⁱ—Pr1—O4	70.88 (10)	C9—N2—Pr1^iv	122.6 (3)
O1—Pr1—O3ⁱⁱ	152.91 (11)	C5—N2—Pr1^iv	133.1 (3)
O6—Pr1—O3ⁱⁱ	72.06 (11)	O2—C1—O1	123.2 (4)
O2ⁱ—Pr1—O3ⁱⁱ	73.82 (11)	O2—C1—C2	117.7 (4)
O4—Pr1—O3ⁱⁱ	106.94 (10)	O1—C1—C2	118.8 (3)
O1—Pr1—O1W	96.60 (11)	C3—C2—C7	120.7 (4)
O6—Pr1—O1W	74.37 (12)	C3—C2—C1	113.5 (4)
O2ⁱ—Pr1—O1W	145.00 (11)	C7—C2—C1	125.7 (4)
O4—Pr1—O1W	75.25 (11)	C2—C3—C4	118.0 (4)
O3ⁱⁱ—Pr1—O1W	108.74 (11)	C2—C3—H3	121.0
O1—Pr1—N2ⁱⁱⁱ	84.24 (11)	C4—C3—H3	121.0
O6—Pr1—N2ⁱⁱⁱ	71.46 (11)	N1—C4—C3	132.5 (4)
O2ⁱ—Pr1—N2ⁱⁱⁱ	76.78 (11)	N1—C4—C5	104.9 (4)
O4—Pr1—N2ⁱⁱⁱ	141.25 (11)	C3—C4—C5	122.5 (4)
O3ⁱⁱ—Pr1—N2ⁱⁱⁱ	83.25 (11)	N2—C5—C6	130.8 (4)
O1W—Pr1—N2ⁱⁱⁱ	137.92 (11)	N2—C5—C4	109.9 (4)
O1—Pr1—O5	75.84 (10)	C6—C5—C4	119.3 (4)
O6—Pr1—O5	50.87 (10)	C7—C6—C5	119.8 (4)
O2ⁱ—Pr1—O5	141.76 (10)	C7—C6—H6	120.1
O4—Pr1—O5	125.30 (10)	C5—C6—H6	120.1
O3ⁱⁱ—Pr1—O5	122.16 (11)	C6—C7—C2	119.7 (4)
O1W—Pr1—O5	67.81 (10)	C6—C7—C8	115.3 (3)
N2ⁱⁱⁱ—Pr1—O5	71.75 (11)	C2—C7—C8	124.8 (4)
O1—Pr1—O4ⁱⁱ	139.88 (10)	O3—C8—O4	119.5 (4)
O6—Pr1—O4ⁱⁱ	86.63 (10)	O3—C8—C7	118.6 (4)
O2ⁱ—Pr1—O4ⁱⁱ	92.78 (10)	O4—C8—C7	121.9 (3)
O4—Pr1—O4ⁱⁱ	70.53 (11)	O3—C8—Pr1ⁱⁱ	57.8 (2)
O3ⁱⁱ—Pr1—O4ⁱⁱ	49.85 (9)	O4—C8—Pr1ⁱⁱ	63.2 (2)
O1W—Pr1—O4ⁱⁱ	67.41 (10)	C7—C8—Pr1ⁱⁱ	165.0 (3)
N2ⁱⁱⁱ—Pr1—O4ⁱⁱ	132.75 (10)	N2—C9—N1	114.0 (4)
O5—Pr1—O4ⁱⁱ	124.59 (9)	N2—C9—H9	123.0
O1—Pr1—C8ⁱⁱ	159.06 (10)	N1—C9—H9	123.0
O6—Pr1—C8ⁱⁱ	75.06 (10)	O5—C10—O6	121.2 (4)
O2ⁱ—Pr1—C8ⁱⁱ	85.58 (10)	O5—C10—C11	121.3 (5)
O4—Pr1—C8ⁱⁱ	91.20 (10)	O6—C10—C11	117.1 (5)
O3ⁱⁱ—Pr1—C8ⁱⁱ	24.71 (10)	O5—C10—C11'	115.5 (10)
O1W—Pr1—C8ⁱⁱ	86.57 (11)	O6—C10—C11'	119.2 (10)
N2ⁱⁱⁱ—Pr1—C8ⁱⁱ	107.21 (11)	C10—C11—H11A	109.5
O5—Pr1—C8ⁱⁱ	124.02 (10)	C10—C11—H11B	109.5
O4ⁱⁱ—Pr1—C8ⁱⁱ	25.55 (10)	H11A—C11—H11B	109.5
C1—O1—Pr1	131.7 (3)	C10—C11—H11C	109.5
Pr1—O1W—H1W	124 (3)	H11A—C11—H11C	109.5
Pr1—O1W—H2W	127 (3)	H11B—C11—H11C	109.5
H1W—O1W—H2W	108 (3)	C10—C11'—H11D	109.5
C1—O2—Pr1ⁱ	148.2 (3)	C10—C11'—H11E	109.5
C8—O3—Pr1ⁱⁱ	97.5 (2)	H11D—C11'—H11E	109.5
C8—O4—Pr1	137.6 (3)	C10—C11'—H11F	109.5
C8—O4—Pr1ⁱⁱ	91.2 (2)	H11D—C11'—H11F	109.5
Pr1—O4—Pr1ⁱⁱ	109.47 (11)	H11E—C11'—H11F	109.5
C10—O5—Pr1	91.6 (3)

O6—Pr1—O1—C1	−171.8 (3)	O2—C1—C2—C3	49.4 (5)
O2ⁱ—Pr1—O1—C1	−32.1 (3)	O1—C1—C2—C3	−124.8 (4)
O4—Pr1—O1—C1	41.1 (3)	O2—C1—C2—C7	−134.6 (4)
O3ⁱⁱ—Pr1—O1—C1	−46.8 (5)	O1—C1—C2—C7	51.3 (6)
O1W—Pr1—O1—C1	112.7 (4)	C7—C2—C3—C4	−1.4 (6)
N2ⁱⁱⁱ—Pr1—O1—C1	−109.6 (4)	C1—C2—C3—C4	174.8 (4)
O5—Pr1—O1—C1	177.8 (4)	C9—N1—C4—C3	−176.2 (5)
O4ⁱⁱ—Pr1—O1—C1	50.3 (4)	C9—N1—C4—C5	1.1 (5)
C8ⁱⁱ—Pr1—O1—C1	15.0 (5)	C2—C3—C4—N1	179.5 (4)
O1—Pr1—O4—C8	58.8 (4)	C2—C3—C4—C5	2.5 (6)
O6—Pr1—O4—C8	−66.6 (4)	C9—N2—C5—C6	178.5 (4)
O2ⁱ—Pr1—O4—C8	144.9 (4)	Pr1^iv—N2—C5—C6	3.1 (7)
O3ⁱⁱ—Pr1—O4—C8	−149.6 (4)	C9—N2—C5—C4	0.0 (5)
O1W—Pr1—O4—C8	−44.1 (4)	Pr1^iv—N2—C5—C4	−175.3 (3)
N2ⁱⁱⁱ—Pr1—O4—C8	109.9 (4)	N1—C4—C5—N2	−0.7 (5)
O5—Pr1—O4—C8	4.3 (4)	C3—C4—C5—N2	177.0 (4)
O4ⁱⁱ—Pr1—O4—C8	−114.9 (4)	N1—C4—C5—C6	−179.3 (4)
C8ⁱⁱ—Pr1—O4—C8	−130.2 (3)	C3—C4—C5—C6	−1.7 (6)
O1—Pr1—O4—Pr1ⁱⁱ	173.75 (13)	N2—C5—C6—C7	−178.6 (4)
O6—Pr1—O4—Pr1ⁱⁱ	48.4 (2)	C4—C5—C6—C7	−0.3 (6)
O2ⁱ—Pr1—O4—Pr1ⁱⁱ	−100.20 (12)	C5—C6—C7—C2	1.3 (6)
O3ⁱⁱ—Pr1—O4—Pr1ⁱⁱ	−34.66 (13)	C5—C6—C7—C8	177.3 (4)
O1W—Pr1—O4—Pr1ⁱⁱ	70.84 (12)	C3—C2—C7—C6	−0.4 (6)
N2ⁱⁱⁱ—Pr1—O4—Pr1ⁱⁱ	−135.22 (14)	C1—C2—C7—C6	−176.2 (4)
O5—Pr1—O4—Pr1ⁱⁱ	119.17 (11)	C3—C2—C7—C8	−176.0 (4)
O4ⁱⁱ—Pr1—O4—Pr1ⁱⁱ	0.0	C1—C2—C7—C8	8.2 (6)
C8ⁱⁱ—Pr1—O4—Pr1ⁱⁱ	−15.29 (12)	Pr1ⁱⁱ—O3—C8—O4	14.5 (4)
O1—Pr1—O5—C10	169.4 (3)	Pr1ⁱⁱ—O3—C8—C7	−163.1 (3)
O6—Pr1—O5—C10	0.2 (3)	Pr1—O4—C8—O3	107.5 (4)
O2ⁱ—Pr1—O5—C10	117.0 (3)	Pr1ⁱⁱ—O4—C8—O3	−13.7 (4)
O4—Pr1—O5—C10	−138.6 (3)	Pr1—O4—C8—C7	−75.0 (5)
O3ⁱⁱ—Pr1—O5—C10	11.5 (3)	Pr1ⁱⁱ—O4—C8—C7	163.8 (3)
O1W—Pr1—O5—C10	−87.3 (3)	Pr1—O4—C8—Pr1ⁱⁱ	121.2 (3)
N2ⁱⁱⁱ—Pr1—O5—C10	80.8 (3)	C6—C7—C8—O3	7.4 (5)
O4ⁱⁱ—Pr1—O5—C10	−49.0 (3)	C2—C7—C8—O3	−176.9 (4)
C8ⁱⁱ—Pr1—O5—C10	−18.0 (3)	C6—C7—C8—O4	−170.1 (4)
O1—Pr1—O6—C10	−13.2 (3)	C2—C7—C8—O4	5.6 (6)
O2ⁱ—Pr1—O6—C10	−128.3 (3)	C6—C7—C8—Pr1ⁱⁱ	−64.3 (11)
O4—Pr1—O6—C10	96.2 (3)	C2—C7—C8—Pr1ⁱⁱ	111.4 (10)
O3ⁱⁱ—Pr1—O6—C10	−170.2 (3)	C5—N2—C9—N1	0.7 (5)
O1W—Pr1—O6—C10	73.6 (3)	Pr1^iv—N2—C9—N1	176.7 (3)
N2ⁱⁱⁱ—Pr1—O6—C10	−81.4 (3)	C4—N1—C9—N2	−1.2 (5)
O5—Pr1—O6—C10	−0.2 (3)	Pr1—O5—C10—O6	−0.4 (5)
O4ⁱⁱ—Pr1—O6—C10	141.1 (3)	Pr1—O5—C10—C11	171.3 (5)
C8ⁱⁱ—Pr1—O6—C10	164.2 (3)	Pr1—O5—C10—C11'	−157.3 (10)
Pr1ⁱ—O2—C1—O1	−128.3 (5)	Pr1—O6—C10—O5	0.4 (5)
Pr1ⁱ—O2—C1—C2	57.8 (7)	Pr1—O6—C10—C11	−171.7 (5)
Pr1—O1—C1—O2	88.8 (5)	Pr1—O6—C10—C11'	156.5 (11)
Pr1—O1—C1—C2	−97.4 (4)

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z; (iii) x, y, z−1; (iv) x, y, z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6^v	0.85 (2)	1.90 (3)	2.712 (5)	159 (5)
O1W—H1W···O2^vi	0.83 (2)	2.06 (3)	2.854 (4)	159 (6)
O1W—H2W···O5^vii	0.84 (2)	1.96 (2)	2.794 (4)	176 (5)

Symmetry codes: (v) x−1, y, z+1; (vi) x+1, y, z; (vii) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	[Pr(C₉H₄N₂O₄)(C₂H₃O₂)(H₂O)]
M_r	422.11
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.4284 (5), 9.0109 (7), 9.7239 (7)
α, β, γ (°)	87.075 (1), 86.498 (1), 84.274 (1)
V (Å³)	645.77 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.81
Crystal size (mm)	0.26 × 0.22 × 0.19

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.386, 0.485
No. of measured, independent and observed [I > 2σ(I)] reflections	3963, 2327, 2184
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.072, 1.04
No. of reflections	2327
No. of parameters	199
No. of restraints	22
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.23, −1.45

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6ⁱ	0.85 (2)	1.90 (3)	2.712 (5)	159 (5)
O1W—H1W···O2ⁱⁱ	0.833 (19)	2.06 (3)	2.854 (4)	159 (6)
O1W—H2W···O5ⁱⁱⁱ	0.836 (19)	1.959 (19)	2.794 (4)	176 (5)

Symmetry codes: (i) x−1, y, z+1; (ii) x+1, y, z; (iii) −x+1, −y, −z.

Acknowledgements

The authors acknowledge the Natural Science Foundation of Guangdong Province (No. 9151063101000037) for supporting this work.

References

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